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Here we represent the first example of the formation of mixed nanoscale associates, constructed from amphiphilic calixresorcinarenes and hydrophobic carboxylic acids including drugs. The amidoamino-calixresorcinarene self-associates effectively solubilize hydrophobic carboxylic acids - drugs such as naproxen, ibuprofen, ursodeoxycholic acid and aliphatic dodecanoic acid - with the formation of the mixed aggregates with the macrocycle/substrate stoichiometry from 1/1 to 1/7. The ionization of organic acids and the peripheral nitrogen atoms of the macrocycles with the subsequent inclusion of hydrophobic acids into the macrocycle self-associates is the driving force of solubilization. In some cases, this leads to the co-assembly of the macrocycle polydisperse associates into supramolecular monodisperse nanoparticles with the diameter of about 100 nm. The efficiency of drug loading into the nanoparticles is up to 45% and depends on the structure of organic acid. The dissociation of the mixed aggregates and release of organic acid are attained by decreasing pH.

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We have prepared four new octaaminoamide resorcin[4]-arenes having hydrocarbon chains of different lengths (1, 2: R = CH 3 ; 3, 4: R = C 11 H 23 ) and different terminal groups (1, 3: NH 2 ; 2, 4: NMe 2 ). The surface tension and self-assembly of aqueous solutions of 2−4 were studied and their critical micelle concentrations (CMC) were determined. At the water/ air interface, compound 2 forms a multilayer structure, whereas compound 3 forms a bilayer and compound 4 a monolayer structure. In addition, we found that compound 3

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